The High-Earner Hobby

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Fact # 1

Sherman presents a typical situation where a high-income taxpayer tries to use large personal expenditures to reduce that income by claiming the expenditures were for a business. In this case a high-income doctor created this homemade website (Op. at 4) called “Songswell.” At the bottom of the front page it says “Site created to showcase music to the world.” And not just any music, but Dr. Sherman’s music. Well, he has the freedom to do that. The site contains various short video clips of various water flows and audio clips of various water sounds. The showcase video is a man riding the “swell” of the ocean. Most of the video clips appear to feature Dr. Sherman playing the guitar and singing songs. The site appears to offer many of these clips for sale but when I clicked on the “buy” buttons I basically got a 404 error (page not found).

The year at issue is 2015. That year, Dr. Sherman worked as an emergency room physician, earning at least $143,000. He failed to file a tax return. In 2019 the IRS prepared a Substitute for Return based on third-party information returns and sent Dr. Sherman an NOD showing a tax deficiency of $60,000. That prompted him to file a return. It reported zero income from Songswell but some $105,00 in expenses, a big chunk of which was for specialized AV equipment, such as $51,000 for a “Alexa Mini Camera” and another $20,000 for “Alex[a] Mini Accessories.” You can watch this YouTube video to see what that system looks like. It’s pretty high-end.

Dr. Sherman petitioned the Tax Court (pro se) and claimed that the NOD was in error because (a) he should be allowed a deduction of $52,500 for expenses associated with his medical practice and (a) he should be allowed a deduction of $105,000 for the net loss he in incurred in Songswell, which he claimed was a business. The medical expense claims are not part of the lesson.

Lesson # 1- Keep Records-Have Income. 

How to build your personal credit

Judge Jones dutifully applies the WTF test and finds that each and every factor weighs against a finding that Songswell was a business. I recommend reading this opinion to get a good sense of how all the factors work. However, two factors were epic fails and give use our first lesson.

The first epic fail was that Dr. Sherman did not conduct the activity in a businesslike manner. That main problem was lack of adequate records. I mean, the man did not even keep basic receipts: “Dr. Sherman was unable to produce any documentation or receipts for most of the expenses listed in the “other” category... Further, although Dr. Sherman purchased some camera equipment and accessories in 2015, the amounts on the receipts do not match the expenses reported on Schedule C. Additionally, many of his equipment purchases occurred outside the 2015 taxable year.” Op. at 6.

But even if he had receipts, a taxpayer needs more than receipts to show they are conducting an activity in a businesslike manner. They need basic records of the business activity. Here, Dr. Sherman had none. He had no records to show a business plan or even to show “when Songswell activities began, nor precisely what activity occurred in taxable year 2015.”  Op. at 11.

The second epic fail was the total lack of income from Songswell and his substantial income from being a doctor. Writes Judge Jones: “His reported losses from Songswell—in addition to his medical practice expenses—would produce a substantial tax benefit, essentially zeroing out any tax obligation he owed.” Op. at 15.

Judge Jones concludes: “This is not a difficult case... Aside from Dr. Sherman’s self-serving testimony that the Songswell activity was conducted for profit, little else counsels in favor of finding a profit motive...” Op. at 10.



Bottom Line #1: Your vanity website is not a business if you have zero sales over multiple years.


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February 12, 2026
When a “Good Year” Still Feels Tight You finally have a year where sales are up and the books show a profit—yet your bank account feels like it missed the memo. You’re working harder than ever, but cash seems to disappear the moment it hits your account. If that sounds familiar, you’re not doing anything wrong—you’re just bumping into one of the most common challenges in business: confusing profit with cash flow. Profit tells you how your business looks on paper.
Cash flow shows how your business feels in real life. And while both matter, only one pays the bills. The Real-World Disconnect Here’s where the confusion usually starts: You invoice a client for $20,000 in December. On your profit and loss statement, that sale boosts your year-end numbers. But if the client doesn’t pay until February, that profit doesn’t do much to help you cover January’s rent, payroll, or taxes. Or imagine a landscaping company that buys $15,000 of equipment in spring to prepare for summer jobs. On paper, the expense is spread out over time—but in reality, that cash leaves your account today. The result? You’re profitable on paper but short on cash in practice. Why This Happens to So Many Business Owners Cash flow issues aren’t a sign of failure—they’re often a natural part of growth. When your business scales, so do your expenses, payment cycles, and timing gaps between money in and money out. The biggest triggers include: Delayed payments: Clients pay on their schedule, not yours.
 Seasonal swings: Slow months still have fixed costs.
 Inventory or supply purchases: You pay upfront, earn later.
 Tax surprises: Profit may be taxable long before the cash arrives.
 Without planning for those timing gaps, even healthy businesses can feel like they’re running on empty. Turning Chaos Into Control This is where working with a trusted financial professional can make all the difference. They can help you: Forecast cash flow so you see slowdowns before they happen.
 Smooth out seasonality by building cash reserves during strong months.
 Review expenses strategically to make sure growth doesn’t outpace available cash.
 Even simple steps—like syncing invoicing and bill-paying schedules or setting aside a percentage of each payment for future expenses—can dramatically reduce stress and improve stability. Bottom Line Profit is your scoreboard. Cash flow is your oxygen.
You need both to survive—and thrive. If your business feels profitable on paper but tight in the bank, you’re not alone. Contact our firm today for guidance on building a cash flow plan that keeps your business strong through every season.
February 11, 2026
Considering bringing on a partner? While there are certainly benefits you want to make sure you consider all aspects of such a relationship and look to the long term. Here are five of the best reasons (Pro’s) to organize a business as a partnership, explained in practical, plainEnglish terms: THE PRO’S 1. Shared Capital and Resources A partnership allows multiple owners to pool money, assets, and resources, making it easier to start or grow a business than going alone. Partners can contribute cash, equipment, property, or intellectual property Reduces the financial burden and risk on any one individual Often improves credibility with lenders and suppliers 2. Complementary Skills and Expertise Partners can bring different strengths and experience to the business. One partner may excel at operations, another at sales or finance Better decisionmaking through multiple perspectives Division of labor increases efficiency and focus This is especially valuable in professional services, startups, and small businesses. 3. Simple and Flexible Structure Partnerships are generally easy to form and operate compared to corporations. Fewer formalities and lower startup costs Minimal ongoing compliance requirements Partnership agreements can be customized to fit the owners’ needs Assets can be moved in and out of the partnership with little or no tax implications. This flexibility allows partners to define roles, profit sharing, and management however they choose. 4. Pass Through Taxation Most partnerships benefit from passthrough taxation, meaning: The partnership itself does not pay federal income tax Profits and losses pass directly on to the partners’ personal tax returns Avoids the “double taxation” faced by many corporations This can simplify tax reporting and, in some cases, reduce the overall tax burden. 5. Shared Risk and Responsibility Running a business involves uncertainty, and partnerships help spread risk. Financial losses are shared according to the partnership agreement Emotional and operational pressure is divided among partners Partners can support each other during difficult periods For many entrepreneurs, not having to shoulder everything alone is a major advantage. THE CON’S Here are five of the strongest reasons not (Con’s) to organize a business as a partnership, especially when compared with an LLC or corporation: 1. Unlimited Personal Liability In a general partnership, each partner is personally liable for the business’s debts and obligations. Personal assets (home, savings, investments) can be seized to satisfy business debts Each partner can be held liable for the actions of other partners One partner’s mistake or lawsuit can financially harm everyone Organizing as a Limited Liability Company (LLC) partnership would limit or may eliminate this personal liability. This is often cited as the single biggest drawback of partnerships. 2. Joint and Several Liability for Partner Actions Each partner acts as an agent of the partnership. One partner can legally bind the business without the others’ consent Poor decisions, negligence, or misconduct by one partner affect all partners Disputes with vendors or customers can expose every partner to risk Even highly trusted partners can unintentionally create legal exposure. 3. Potential for Conflict and Management Disputes Partnerships often fail due to internal disagreements, not business performance. Differences in work ethic, vision, or priorities can cause tension Decisionmaking authority may be unclear or contested Resolving disputes can be costly and disruptive Without a strong partnership agreement, disagreements can quickly escalate. 4. Limited Continuity and Stability Most partnerships lack perpetual existence. The partnership may automatically dissolve if a partner leaves, retires, becomes disabled, or dies Ownership transfers are often restricted or complicated Investors and lenders may view partnerships as less stable This can make longterm planning and growth more difficult. 5. Harder to Raise Capital and Attract Investors Partnerships are often less attractive to outside investors. No easily transferable ownership interests like corporate stock Investors may avoid exposure to partnership liability Growth options are more limited compared to LLCs or corporations As a result, partnerships can struggle to scale beyond a certain size. The Agreement A key factor in any successful partnership is its operating/partnership agreement. A good agreement will lay out specific information, purpose, requirements, expectations, responsibilities, how much capital is to be raised and by whom, allocations of profits, losses and distributions, duties and obligations of the partners to the partnership and each other, possible compensation, how new partners are let in and how partners are allowed to withdrawal. You must also consider possible issues that may happen and have a contingency plan to address such things as; how partnership interests are handled, dissolution of the partnership, dispute amongst partners resolution and other items must be addressed in the agreement should a problem arise. Such an agreement can be a very complex document due to all the things that should be addressed so consulting an attorney knowledgeable in partnership law is crucial. Each state has its own requirements thus the attorney needs to make sure the agreement will comply. Also, the IRS itself has things which it wants to see in the agreement. Before any operating/partnership agreement is signed, it should be reviewed by an attorney, each of the partners and a tax professional to see that it is in compliance with all rules and regulations and the partners, themselves, agreed to be bound by it. Before you make the final decision on whether a partnership structure is right for you and your business associates, sit down with a tax professional and an attorney to discuss each of these good and bad reasons. Looking for a financial partnership that thrives on building strong relationships with their clients? Call Steven Brewer today at 812-883-6938 to schedule an appointment. Accountability and results in growing your business.
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February 5, 2026
Discover how pay-as-you-go workers comp insurance improves cash flow, boosts accuracy, and simplifies payroll for small businesses. Learn how it works.